


Flirting With Death- A Dean x Death smut fanfic

by Impala69



Category: Supernatural
Genre: Death (Supernatural) Loves Fast Food, Fluff and Smut, Humour, Hurt Dean Winchester, M/M, Possessive Dean Winchester, References to Supernatural (TV), Shameless Smut
Language: English
Status: In-Progress
Published: 2019-09-15
Updated: 2019-09-18
Packaged: 2020-10-19 10:48:19
Rating: Not Rated
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 2
Words: 2,700
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20655986
Author URL: https://archiveofourown.org/users/Impala69/pseuds/Impala69
Summary: Dean Winchester has always flirted with Death, whether in the metaphorical sense or the literal sense, but what happens when he pushes the entity of death for more than just a common brush with death?Has Dean Winchester finally bit off more than he can chew?What makes him so attracted to the fourth Horseman of the apocalypse and most importantly  why can’t he stop pestering him?





	1. Son Of A Bitch!

**Author's Note:**

> Hi this is my first fanfic on AO3 I wanted to contribute to the tiny ship that is Dean and Death I thought the characters had really good chemistry In then TV series. This has been on my phone for a while so I’ve decided to post it. Excuse the horrible butchering of this the English language. Stay tuned babes. Don’t forget kudos and comments if you like what I write.

When you’ve visited Hell’s Kitchen as much as I have seeing the Grim Reaper turns from a terrifying experience into a Sunday night dinner date.

I mean he’s a frightening being, always has been, older than God, purger of souls, it may seem like a pretty damn stupid idea, but I’ve always flirted with death one way or another why stop now?

All I know is this is going to be one hell of a ride.

Crack!

“Ahhhhhh!”

SQUELCH!

A distant voice seemed to cascade in the back of Deans head barely pushing through the oncoming darkness.

“DEAN!!”

Sammy is that you?

THUD!

Dean Winchester for the 60th time today has been murdered.

“ Son of a bitch.” Dean groaned into the expensive carpet his fist slamming against the Persian carpet. 

“ Dean...I told you not to come back here.” A velvet voice tickles his ear, it’s threatening undertone like aged whiskey sitting in Deans gut sending a pleasant shiver down his back as he pulled his face off the lush carpet.

He looked at the man sitting in front of him, dressed so elegantly drinking in his appearance like a sober mans first drop of alcohol.

Hair slicked back, a gaunt appearance and cheek bones sharper than knives.

Suit blacker than the impala, frame slender and powerful he couldn’t help admire the man.

Who quite obviously took pleasure in ignoring Deans gaze.

“ Want a tip? Never trust an axe murderer.” Dean groaned pushing himself up off the floor into sitting position.

“ They will stab you in the back, literally.”

A warm and unusual sound graced Deans ears he heard the rare chuckle erupt from the man in front of him.

“ For such an insignificant fleeting creature I always delight in your jokes Dean.” A smile spread across Deaths lips.

“ Now to decide whether to send you back or keep you here forever, shackle you to this confounded place.”

Tension seemed to fill the air, it heavily pressed on both their shoulders.

“ Well if you wanted to do the whole ball and chain routine, I mean take me out to dinner first.” Dean grimaced as he held his stomach his eyes lulling and blurring as they focus on the carpet.

The soft scrape of a chair being pushed back echoed in the room, black hand crafted Italian leather shoes came into his view.

He looked up a hand outstretched in his direction, a very nice looking hand if Dean had said so himself. He pressed his hand into the friendly gesture of support, the warmth of Deans hand was pleasantly cooled by the hand of his companion.

“ Did anyone tell you your mouth could get you into trouble Dean.” A hiss came from the man above.

“ Well my mouth can do other things that can get me into even more trouble give me some credit I ju-.” Dean said grinning, his next sentence cut short as he was yanked to his feet effortlessly.

Chest colliding with chest, a hand wrapping so gently around Deans waist scorched his skin making his body arch against his companion.

A heated lip pressed against Deans sensitive ear making the tips of his ear burn.

“ Dean...I’m very old, quite old. So when you play these games know that I’m not amused so be good!”

There was very few men in his life that Dean Winchester listened to, it was either because they frightened him or he respected them in this case Death was capable of both however right now at this very moment another unexpected thing had come into play.

L U S T

“ I’m well aware you could have dodged that minuscule maggot and yet here you are again in my lands, at my desk dying to be here. Why are you here Dean?”

Deans mouth felt like he hadn’t spoken in twelve years, his throat tasted like saw dust and dirt.

“ I, I j-just...”

“ Say it!” The grim Reaper sneered.

“ I wanted to see you.” Dean Winchester choked out, his voice shaking as he voiced his real intentions for the first time in a very long time.

“ Mmm Dean I do enjoy it when you’re more honest.” The mans voice practically purred making Deans knees turn to jello. “Go on you know what I like... beg.” 

Something hard and throbbing pressed into Deans core and his throat tightened in response.

“ P-please.” Dean said that one word, dripping with sheer desperation as his pants had become quite uncomfortable as they tightened painfully.


	2. I Confess

**Notes for the Chapter:**

> Honestly this is a lot more soppy than how I usually write my stories babes. But being a fan of SPN and seeing what Dean goes through I guess my soft hearted self in the end just wants to write Dean with something happy. Don’t forget kudos and comments it makes me happy reading them pals. If you liked this story check out my other fanfic -A Debt To Be Paid. It’s a lot longer.

“I..” words seem to dry up In his mouth like an Arizona desert. 

“Well use your big boy words Dean, I’m listening.” The tone was mocking. 

Dean took in a shaky nervous breath, which proved to be a big mistake. 

He could smell it, primroses, the man smelt of primroses and a rather strange but delicious combination of pickle chips as though he had just been eating a bag.

Which left Dean salivating, for the chips or the man he was unsure of but he knew he needed more, as he did the unspeakable, in all his years he didn’t know what made him have such brass balls for the next action, maybe the axe had hit him harder than he thought.

He leaned against the man and buried his nose into the collar of his shirt taking in that agonising scent like an addict his hands wrapping around the man’s frail back and pulling him closer. 

“You just smell so good.” He said absent minded in his actions as he pressed himself closer his nose touching the delicate skin of the man’s throat.

Only when the man tense underneath him did he come to the conclusion that maybe it wasn’t a good idea to man handle the embodiment of death.

“Of all the arrogant insects...” the man began, his voice shaking slightly. 

You’ve done it now Dean. He thought to himself, whatever had happened between them it had always been on Deaths terms and who in their right mind would question that? 

He took a step back seeing the quiet seething rage on the man’s face, he backed away as the man descended on him slowly his voice as venomous as a king cobra. 

“Unsightly, insignificant.” The man’s insults spilled from his lips like black ink across a parchment.

“Ameba that I have ever come across, who dared..” 

For the first time Dean felt real fear of something in his life, it coiled up his spine and kissed at his heartbeat making it go faster. 

The more the man came closer the more he backed away it was like a dance, before his back finally hit the wooden mahogany of a doorframe.

“To so much as overstep...”

A hand as cold as snow touched his shoulder and he felt his knees crumpling underneath him, but not once did his eyes leave Deaths. 

“Do you have any words before I expel the only thing inside you that makes you Dean Winchester and leave behind only an empty shell you...lowly... parasite. ” 

The man in front of him had eyes like the darkest shots of whiskey, they would have been terrifying to other people at its raven blackness but to Dean they were... they were..

“Fuck you’re so damn beautiful...” He admitted out loud. 

Death hesitates he stood there his hands that have taken more lives in existence since the dawn of time, was hesitating. 

Dean grasped the hand that held his shoulder and kept him on his knees pulling it to his lips and delicately pressing his mouth to those soft long fingers.

He pressed his forehead in a rare show of a sentimental gesture, his breath ragged as he closed his eyes awaiting his judgment. 

Silence filled the room like an unwelcome guest, fear prickled at Deans skin like a thousand needles but also something beyond that a serene sense of calmness.

He waiting for the finishing blow. 

But it never came. 

He looked upwards and it seemed as though Death was well and truly frozen to the spot, no quips, mocking, the anger all but resolved into a very puzzled expression seemingly permanently fixated on the man’s features. 

The sincerity of Deans actions had left the poor entity in quite a stupor, he had not expected such blind truthfulness.

Dean once realising after a few awkward minutes that the beautiful creature in front of him was somewhat incapable of speaking at this very minute, he cleated his throat and decided to press his luck and come clean.

He stood on his feet holding the man’s hand firmly in his another hand on his shoulder as he steered the man backwards towards his study.

He wet his throat and prepared to say one of the most foolish things he ever had said.

“You’re right I have been dying on purpose, I guess it’s a bit obvious when I’m here every other Tuesday like it’s a damn motel.” 

He gently squeezed the man’s shoulder as he tried to inject humour into this bizarre and untimely confession. 

“You want to know the truth?” 

His voice shook slightly as he pressed on, Winchester’s had never been good at expressing their feelings and whatever this was he certainly didn’t get it from his father.

“I want you so bad.” His voice squeezed almost painfully as he pushed against the lump in his throat.

“Not just like on a Saturday night because I jump in front of an axe murderer either! I can tell you right now that was not fun.” 

They backed away further, his hands leading the poor shaken man closer towards his desk.

“I want to sleep with you through the night not just a quickie, I want to hold you close, so close there isn’t even a damn gap between us.” 

The soft pitter patter of shoes against carpet followed by a soft shuffling. 

“I want to curl you against me until morning comes with my hands in your god damn gorgeous hair, I want to..”

Each confession seemed to breath life back into the poor stunned man that Dean held as they bumped clumsily into Deaths desk, his pens messily scattering all over the carpet floor as Death braced his hands against the desk.

Deans hands tenderly moved from Deaths shoulder to cup at the being cheek both his hands tenderly embracing the man’s face.

“I want to fucking go out with you in the morning and eat a burger, a terrible strawberry milkshake and pickle chips at some greasy, crappy food cart that’s got like a one star rating.” 

Deans callused fingers stroking along the fine cheek bones of the man underneath him.

“I want to kiss the daylights out of you in the back of my impala, talk with you, eat with you, cook you a really bad meal at my place at midnight because neither of us can sleep, to be fair I suck at cooking we’d probably have to order take out afterwards.”

Laughter burst into Deans chest and it sounded truly happy, the corners of his eyes crinkling. 

I fucking want it all. All of you.” 

His voice shaking as a wetness appeared in Deans eyes, the vulnerability of a man that’s never truly had the chance to be human but was looking at Death with more love and insecurity that he’s even been given himself.

“D-Dean I.” Death stuttered. 

A wet droplet suddenly rolled down Deaths cheek, but it wasn’t Death that was crying, the lashes of Dean Winchester has tears on them like snow crystals.

“Don’t say anything, unless it’s yes.” Dean said his voice hoarse. 

“D-Dean!” 

“Mmph.” Lips smeared against Deaths in an intimate embrace making whatever words the man Dean was kissing lost on their lips, the soft crush of lips against lips. As Dean Winchester put everything into this kiss that Winchester’s weren’t meant to say and he prayed that he’d understand. 

It was hurt, love, hope, begging, demanding all in one. Rough and harsh intimate and soft and all encompassing a question, posed towards the man and it said ‘please be mine?’

Death could stop this, there was precisely at least 10,000 ways in which he could stop this and 99% of them would be ending it quite gruesomely for someone of a species he would normally regard as a cockroach on his lobster, the lonely, long suffering human race which always found some way to survive. 

But out of all of them only one answer seemed logical. He curled his hands desperately into Dean Winchester’s hair one at his neck quite threateningly and one at his nape.

A guttural whimper came from Dean, who was anything but a coward. 

This was the make or break answer.

Death looked into the baby blue eyes of this broken and wounded man, whose only constant in his life was misery, death and destruction and returned the kiss with a fevered desperation.

“Mmmm mmmm.”

His lips tumbling over Deans own sweet mouth, Dean tasted like bad take out, mint juleps which did an extremely poor job of covering up the taste of cheap home brewed alcohol paired with the velvet finishing taste of something that could only be well and truly described as Dean.

Death found one of his hands clutching at Deans raggedy old leather jacket holding him in place quite firmly. He smelt like leather, mints and whiskey to Death anyone else would have been repulsive. 

But Dean Winchester was anything but repulsive to him much to his own grievance he was quite the opposite, Death found himself foolishly giving him more leeway than any other creature in existence. 

Give a Dean a inch and he will take a mile. 

Dean gathered the fragile man into his arms his hands grasping those delicate hips and curling into the bone as he lifted him on his own desk, his arms resting on either side of the man trapping him as he luxuriously took time exploring his mouth nipping the gentle flesh making the poor creature underneath him quiver and arch his back beautifully. 

A tongue prodded at Deaths lips and he cautiously opened his mouth further awaiting to see what Dean would do.

Dean nearly cried with relief as he felt this soft lips open invitingly and not one to turn down a invitation his tongue swept into the smaller man’s mouth tasting the full extent of his flavour. 

Deaths eyes fluttered shut as a pleased sound drifted from his chest his tongue being swept across by Deans, his nails scratching slightly at the back of Deans scalp who grunted in satisfaction.

Dean kissed him quite bruising, forcing colour into those lifeless lips and ambrosia into his bones. 

The soft squelch of his tongue slicking against Deaths did things to the organ between his legs who was well and truly awake. 

When they finally had to break apart for breath, which was Death being quite considerate of Deans very human need to breathe the sight that met Dean was like Christmas in July. 

Deaths hand did not leave Deans jacket as though he was fearful Dean would run away as Deans eyes swept over him. 

Death was known to be quite a suave looking creature, his hair was always perfectly slicked back, not a single hair out of place, his suit was always without a single crinkle and he held himself with a most elegant regard and perfect posture.

But the Death that was sitting on his own desk with his pencils scrawled about the place was a very different man. 

His lips were swollen and reddened from Deans insistent kissing and biting, his cheeks were flushed and his eyes dark pools of lust.   
His hair stuck out at very unusual angles and his shirt had at least lost two buttons in their struggle and when he looked downwards the proof of Deaths arousal jutted in his black business pants painfully. 

Dean licked his lips fixated on that delicious looking package. 

“Dean?” His deep voice heavy with lust and barely restricted desire.

“Yeah.” Dean Spike bewitched by the man as his attention snapped but upwards meeting Deaths beautiful coffee coloured orbs. 

“Bedroom, left, now.”

It wasn’t a question but an order.

**Notes for the Chapter:**

> Don’t forget kudos and comments this was a particularly long chapter. But I’d feel bad about breaking it up, it would ruin the flow of the story. Thanks babes.

**Author's Note:**

> Kudos and comments please loves, cheers.


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